N-(Pyridin-2-yl) arylsulfonamide inhibitors of 11β-hydroxysteroid dehydrogenase type 1: Discovery of PF-915275

Bioorganic and Medicinal Chemistry Letters

Volumn 19, Issue 13, 2009, Pages 3493-3497

  Siu, Michael ^a   Johnson, Theodore O ^a   Wang, Yong ^a   Nair, Sajiv K ^a   Taylor, Wendy D ^a   Cripps, Stephan J ^a   Matthews, Jean J ^a   Edwards, Martin P ^a   Pauly, Thomas A ^a   Ermolieff, Jacques ^a   Castro, Arturo ^a   Hosea, Natilie A ^a   LaPaglia, Amy ^a   Fanjul, Andrea N ^a   Vogel, Jennifer E ^a  

^a PFIZER INC   (United States)

Author keywords

11 Hydroxysteroid dehydrogenase; Diabetes; Lipophilic efficiency; PF 915275

Indexed keywords

11BETA HYDROXYSTEROID DEHYDROGENASE 1; PF 915275; SULFONAMIDE;

ANIMAL CELL; AREA UNDER THE CURVE; ARTICLE; CELL STRAIN HEK293; CONCENTRATION RESPONSE; CONTROLLED STUDY; CRYSTAL STRUCTURE; DIABETES MELLITUS; DOG; DRUG CLEARANCE; DRUG HALF LIFE; DRUG POTENCY; ENZYME INHIBITOR INTERACTION; GUINEA PIG; HEPATOMA CELL; HUMAN; HUMAN CELL; LIPOPHILICITY; METABOLIC SYNDROME X; MONKEY; NONHUMAN; PHYSICAL CHEMISTRY; RAT; STEROIDOGENESIS;

11-BETA-HYDROXYSTEROID DEHYDROGENASE TYPE 1; AMINOPYRIDINES; ANIMALS; CELL LINE; COMPUTER SIMULATION; CRICETINAE; CRYSTALLOGRAPHY, X-RAY; DRUG DESIGN; ENZYME INHIBITORS; HUMANS; RATS; STRUCTURE-ACTIVITY RELATIONSHIP; SULFONAMIDES;

EID: 66749093622     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2009.05.011     Document Type: Article

References (44)

1. Tomlinson J.W., Walker E.A., Bujalska I.J., Draper N., Lavery G.G., Cooper M.S., Hewison M., and Stewart P.M. Endocr. Rev. 25 (2004) 831
2. Seckl J.R., and Walker B.R. Trends Endocrinol. Metab. 15 (2004) 418
3. Tomlinson J.W., and Stewart P.M. Drug Discovery Today Ther. Strateg. 2 (2005) 93
4. Wamil M., and Seckl J.R. Drug Discovery Today 12 (2007) 504
5. Consoli A., Nurjhan N., Capani F., and Gerich J. Diabetes 38 (1989) 550
6. Barf T., Vallgårda J., Emond R., Häggstroem C., Kurz G., Nygren A., Larwood V., Mosialou E., Axelsson K., Olsson R., Engblom L., Edling N., Rönquist-Nii Y., Öhman B., Alberts P., and Abrahmsén L. J. Med. Chem. 45 (2002) 3813
7. Coppola G.M., Kukkola P.J., Stanton J.L., Neubert A.D., Marcopulos N., Bilci N.A., Wang H., Tomaselli H.C., Tan J., Aicher T.D., Knorr D.C., Jeng A.Y., Dardik B., and Chatelain R.E. J. Med. Chem. 48 (2005) 6696
8. Xiang J., Ipek M., Suri V., Massefski W., Pan N., Ge Y., Tam M., Xing Y., Tobin J.F., Xu X., and Tam S. Bioorg. Med. Chem. Lett. 15 (2005) 2865
9. Olson S., Aster S.D., Brown K., Carbin L., Graham D.W., Hermanowski-Vosatka A., LeGrand C.B., Mundt S.S., Robbins M.A., Schaeffer J.M., Slossberg L.H., Szymonifka M.J., Thieringer R., Wright S.D., and Balkovec J.M. Bioorg. Med. Chem. Lett. 15 (2005) 4359
10. Gu X., Dragovic J., Koo G.C., Koprak S.L., LeGrand C., Mundt S.S., Shah K., Springer M.S., Tan E.Y., Thieringer R., Hermanowski-Vosatka A., Zokian H.J., Balkovec J.M., and Waddell S.T. Bioorg. Med. Chem. Lett. 15 (2005) 5266
11. Yeh V.S.C., Kurukulasuriya R., Madar D., Patel J.R., Fung S., Monzon K., Chiou W., Wang J., Jacobson P., Sham H.L., and Link J.T. Bioorg. Med. Chem. Lett. 16 (2006) 5408
12. Yeh V.S.C., Patel J.R., Yong H., Kurukulasuriya R., Fung S., Monzon K., Chiou W., Wang J., Stolarik D., Imade H., Beno D., Brune M., Jacobson P., Sham H., and Link J.T. Bioorg. Med. Chem. Lett. 16 (2006) 5414
13. Yeh V.S.C., Kurukulasuriya R., Fung S., Monzon K., Chiou W., Wang J., Stolarik D., Imade H., Shapiro R., Knourek-Segel V., Bush E., Wilcox D., Nguyen P.T., Brune M., Jacobson P., and Link J.T. Bioorg. Med. Chem. Lett. 16 (2006) 5555
14. Sorensen B., Rohde J., Wang J., Fung S., Monzon K., Chiou W., Pan L., Deng X., Stolarik D., Frevert E.U., Jacobson P., and Link J.T. Bioorg. Med. Chem. Lett. 16 (2006) 5958
15. Richards S., Sorensen B., Jae H., Winn M., Chen Y., Wang J., Fung S., Monzon K., Frevert E.U., Jacobsen P., and Link J.T. Bioorg. Med. Chem. Lett. 16 (2006) 6241
16. St. Jean Jr. D.J., Yuan C., Bercot E.A., Cupples R., Chen M., Fretland J., Hale C., Hungate R.W., Komorowski R., Veniant M., Wang M., Zhang X., and Fotsch C. J. Med. Chem. 50 (2007) 429
17. Rodhe J.J., Pliushchev M.A., Sorensen B.K., Wodka D., Shuai Q., Wang J., Fung S., Monzon K.M., Chiou W.J., Pan L., Deng X., Chovan L.E., Ramaiya A., Mullally M., Henry R.F., Stolarik D.F., and Imade H.M. J. Med. Chem. 50 (2007) 149
18. Sorensen B., Winn M., Rohde J., Shuai Q., Wang J., Fung S., Monzon K., Chiou W., Stolarik D., Imade H., Pan L., Deng X., Chovan L., Longenecker K., Judge R., Qin W., Brune M., Camp H., Frevert E.U., Jacobson P., and Link J.T. Bioorg. Med. Chem. Lett. 17 (2007) 527
19. Patel J.R., Shuai Q., Dinges J., Winn M., Pliushchev M., Fung S., Monzon K., Chiou W., Wang J., Pan L., Wagaw S., Engstrom K., Kerdesky F.A., Longenecker K., Judge R., Qin W., Imade H.M., Stolarik D., Beno D.W.A., Brune M., Chovan L.E., Sham H.L., Jacobsen P., and Link J.T. Bioorg. Med. Chem. Lett. 17 (2007) 750
20. Webster S.P., Ward P., Binnie M., Craigie E., McConnell K.M.M., Sooy K., Vinter A., Seckl J.R., and Walker B.R. Bioorg. Med. Chem. Lett. 17 (2007) 2838
21. Flyrén K., Bergquist L.O., Castro V.M., Fotsch C., Johansson L., St. Jean Jr. D.J., Sutin L., and Williams M. Bioorg. Med. Chem. Lett. 17 (2007) 3421
22. Xiang J., Ipek M., Suri V., Tam M., Xing Y., Huang N., Zhang Y., Tobin J., Mansour T.S., and McKew J. Bioorg. Med. Chem. 15 (2007) 4396
23. Sutin L., Andersson S., Bergquist L., Castro V.M., Danielsson E., James S., Henriksson M., Johansson L., Kaiser C., Flyrén K., and Williams M. Bioorg. Med. Chem. Lett. 17 (2007) 4837
24. Yuan C., St. Jean Jr. D.J., Liu Q., Cai L., Li A., Han N., Moniz G., Askew B., Hungate R.W., Johansson L., Tedenborg L., Pyring D., Williams M., Hale C., Chen M., Cupples R., Zhang J., Jordan S., Bartberger M.D., Sun Y., Emery M., Wang M., and Fotsch C. Bioorg. Med. Chem. Lett. 17 (2007) 6056
25. Aster S.D., Graham D.W., Kharbanda D., Patel G., Ponpipom M., Santorelli G.M., Szymonifka M.J., Mundt S.S., Shah K., Springer M.S., Thieringer R., Hermanowski-Vosatka A., Wright S.D., Xiao J., Zokian H., and Balkovec J.M. Bioorg. Med. Chem. Lett. 18 (2008) 2799
26. Johansson L., et al. J. Med. Chem. 51 (2008) 2933
27. Wang H., Ruan Z., Li J.J., Simpkins L.M., Smirk R.A., Wu S.C., Hutchins R.D., Nirschl D.S., Kirk K.V., Cooper C.B., Sutton J.C., Ma Z., Golla R., Seethala R., Salyan M.E.K., Nayeem A., Krystek Jr. S.R., Sheriff S., Camac D.M., Morin P.E., Carpenter B., Robl J.A., Zahler R., Gordon D.A., and Hamann L.G. Bioorg. Med. Chem. Lett. 18 (2008) 3168
28. Zhu Y., Olson S.H., Hermanowski-Vosatka A., Mundt S., Shah K., Springer M., Thieringer R., Wright S., Xiao J., Zokian H., and Balkovec J.M. Bioorg. Med. Chem. Lett. 18 (2008) 3405
29. Zhu Y., Olson S.H., Graham D., Patel G., Hermanowski-Vosatka A., Mundt S., Shah K., Springer M., Thieringer R., Wright S., Xiao J., Zokian H., Dragovic J., and Balkovec J.M. Bioorg. Med. Chem. Lett. 18 (2008) 3412
30. Sun D., Wang Z., Di Y., Jaen J.C., Labelle M., Ma J., Miao S., Sudom A., Tang L., Tomooka C.S., Tu H., Ursu S., Walker N., Yan X., Ye Q., and Powers J.P. Bioorg. Med. Chem. Lett. 18 (2008) 3513
31. Julian L.D., Wang Z., Bostick T., Caille S., Choi R., DeGraffenreid M., Di Y., He X., Hungate R.W., Jaen J.C., Liu J., Monshouwer M., McMinn D., Rew Y., Sudom A., Sun D., Tu H., Ursu S., Walker N., Yan X., Ye Q., and Powers J.P. J. Med. Chem. 51 (2008) 3953
32. Xiang J., Wan Z., Li H., Ipek M., Binnun E., Nunez J., Chen L., McKew J.C., Mansour T.S., Xu X., Suri V., Tam M., Xing T., Li X., Hahm S., Tobin J., and Saiah E. J. Med. Chem. 51 (2008) 4068
33. Reviews of patent applications:. Fotsch C., Askew B., and Chen J.J. Expert Opin. Ther. Patent 15 (2005) 289
34. Webster S.P., and Pallin T.D. Expert Opin. Ther. Patent 17 (2007) 1407
35. Castro A., Zhu J.X., Alton G.R., Rejto P., and Ermolieff J. Biochem. Biophys. Res. Commun. 357 (2007) 561
36. Protein Data Bank: 3G49
37. 4S m/z: 410.0941; Found: 410.0936.
38. Goto J., Sakane K., Nakai Y., Teraji T., and Kamiya T. J. Antibiot. 37 (1984) 532
39. Shimizu T., Osako K., and Nakata T. Tetrahedron Lett. 38 (1997) 2685
40. Prepared following the method described for the synthesis of ethyl [6-(3-chloro-2-methylbenzenesulfonyl-amino)-pyridin-2-yl] acetate (9) using the appropriate starting materials.
41. Hopkins A.L., Groom C.R., and Alex A. Drug Discovery Today 9 (2004) 430
42. Bujalska I., Shimojo M., Howie A., and Stewart P.M. Steroids 62 (1997) 77
43. Bhat B.G., Hosea N., Fanjul A., Herrera J., Chapman J., Thalacker F., Stewart P.M., and Rejto P.A. J. Pharmacol. Exp. Ther. 324 (2008) 299
44. Courtney R., Stewart P.M., Toh M., Ndongo M., Calle R.A., and Hirshberg B. J. Clin. Endocrinol. Metab. 93 (2008) 550